CN106597808B - Photosensitive resin composition, photosensitive resin film and color filter - Google Patents

Photosensitive resin composition, photosensitive resin film and color filter Download PDF

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CN106597808B
CN106597808B CN201610872578.5A CN201610872578A CN106597808B CN 106597808 B CN106597808 B CN 106597808B CN 201610872578 A CN201610872578 A CN 201610872578A CN 106597808 B CN106597808 B CN 106597808B
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chemical formula
photosensitive resin
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resin composition
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CN106597808A (en
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金昭贤
权才暎
金善大
金智恩
徐光源
崔承集
崔恩晶
韩圭奭
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Samsung SDI Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B55/00—Azomethine dyes
    • C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/40—Treatment after imagewise removal, e.g. baking

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Optics & Photonics (AREA)
  • Materials For Photolithography (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Optical Filters (AREA)

Abstract

The present invention provides a photosensitive resin composition, a photosensitive resin film manufactured by using the photosensitive resin composition, and a color filter comprising the photosensitive resin film, wherein the photosensitive resin composition comprises: (A) a binder resin; (B) dyes consisting of cations and anions; (C) a photopolymerizable compound; (D) a photopolymerization initiator; and (E) a solvent, wherein the dye is contained in an amount of 15 to 40 wt% based on the total amount of the photosensitive resin composition and the cation is represented by chemical formula 1. The photosensitive resin composition of the invention can provide a color filter with excellent brightness, heat resistance, chemical resistance and light resistance. [ chemical formula 1]

Description

Photosensitive resin composition, photosensitive resin film and color filter
Cross Reference to Related Applications
This application claims priority and benefit of korean patent application No. 10-2015-0143593, filed on korean intellectual property office at 10/14/2015, the entire contents of which are incorporated herein by reference.
Technical Field
The invention relates to a photosensitive resin composition, a photosensitive resin film using the same and a color filter.
Background
A great deal of research on preparing pigments having uniformly sized particles is to treat the pigments after synthesis via processes such as salt milling to contribute to a stable dispersion state and refinement of the pigment dispersion. In addition, since pigments are limited in brightness and contrast due to particle size, but a color image sensor of an image sensor requires a much smaller particle diameter of a dispersion, research on improving brightness, contrast, etc. has been conducted by using not pigments alone but a mixture with dyes as a hybrid colorant.
However, the hybrid colorant has not been reported to show excellent effects in improving characteristics such as heat resistance and brightness, as compared to conventional colorants.
Therefore, it is necessary to study a suitable compound as a colorant for a photosensitive resin composition.
Disclosure of Invention
One embodiment provides a photosensitive resin composition.
Another embodiment provides a photosensitive resin film manufactured using the photosensitive resin composition.
Still another embodiment provides a color filter including the photosensitive resin film.
One embodiment provides a photosensitive resin composition comprising: (A) a binder resin; (B) dyes consisting of cations and anions; (C) a photopolymerizable compound; (D) a photopolymerization initiator; and (E) a solvent, wherein the dye is included in an amount of 15 to 40 wt% based on the total amount of the photosensitive resin composition, and the cation is represented by chemical formula 1.
[ chemical formula 1]
Figure BDA0001124609760000021
In the chemical formula 1, the first and second,
R1to R6Independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group,
R7is a substituted or unsubstituted C6 to C20 aryl group, and
x is-O-, -S-or-NR8-(R8Is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group).
X may be-O-or-S-.
R1To R4May independently be a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.
The cation may be represented by chemical formula 2.
[ chemical formula 2]
Figure BDA0001124609760000022
In the chemical formula 2, the first and second organic solvents,
R9and R10Independently a substituted or unsubstituted C1 to C20 alkyl group,
R11and R12Independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R13is a substituted or unsubstituted C6 to C20 aryl group,
R14to R17Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
n1 to n4 are independently integers in the range of 0 to 5, 0. ltoreq. n1+ n 2. ltoreq.5 and 0. ltoreq. n3+ n 4. ltoreq.5, and
x is-O-or-S-.
The cation may be represented by a selected one of chemical formulas 3 to 7.
[ chemical formula 3]
Figure BDA0001124609760000031
In the chemical formula 3, the first and second,
R18、R19and R21Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
[ chemical formula 4]
Figure BDA0001124609760000032
In the chemical formula 4, the first and second organic solvents,
R18to R21Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
[ chemical formula 5]
Figure BDA0001124609760000041
In the chemical formula 5, the first and second organic solvents,
R18and R19Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R27is a substituted or unsubstituted C6 to C20 aryl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
[ chemical formula 6]
Figure BDA0001124609760000042
In the chemical formula 6, the first and second,
R18and R19Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R27and R28Independently a substituted or unsubstituted C6 to C20 aryl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
[ chemical formula 7]
Figure BDA0001124609760000051
In the chemical formula 7, the first and second,
R18、R19and R21Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R28is substituted byOr unsubstituted C6 to C20 aryl,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
The cation may be represented by a selected one of chemical formulas 5-3, 5-4, 5-5, 5-6, 7-8, 7-10, 7-12, 7-14, and 7-17.
[ chemical formulas 5-3]
Figure BDA0001124609760000052
[ chemical formulas 5-4]
Figure BDA0001124609760000061
[ chemical formulas 5 to 5]
Figure BDA0001124609760000062
[ chemical formulas 5 to 6]
Figure BDA0001124609760000071
[ chemical formulae 7 to 6]
Figure BDA0001124609760000072
[ chemical formulae 7 to 8]
Figure BDA0001124609760000073
[ chemical formulae 7 to 10]
Figure BDA0001124609760000081
[ chemical formulas 7-12]
Figure BDA0001124609760000082
[ chemical formulae 7 to 14]
Figure BDA0001124609760000091
[ chemical formulae 7 to 17]
Figure BDA0001124609760000092
The anion may be represented by a selected one of formulas a to F.
[ chemical formula A ]
Figure BDA0001124609760000093
[ chemical formula B ]
Figure BDA0001124609760000094
[ chemical formula C ]
PW12O40 3-
[ chemical formula D ]
SiW12O40 4-
[ chemical formula E ]
CF3SO3 -
[ chemical formula F ]
C1O4 -
The dye may be a blue dye.
The dye may have a maximum absorbance (λ) in a wavelength of 600 nm to 700 nmmax)。
The dye may have a maximum transmittance (T) in a wavelength of 400 nm to 500 nmmax)。
The photosensitive resin composition may further include a pigment.
The binder resin may have a weight average molecular weight of 5,000 g/mole to 15,000 g/mole.
The binder resin may have an acid value of 80 to 130 milligrams of potassium hydroxide per gram (mgKOH/g).
The binder resin may include acryl-based binder resin (acryl-based binder resin), cardo-based binder resin (cardo-based binder resin), or a combination thereof.
The photosensitive resin composition may include 1 to 30% by weight of the binder resin (a) based on the total amount of the photosensitive resin composition; 15 to 40% by weight of a dye (B); 1 to 15% by weight of a photopolymerizable compound (C); 0.01 to 10% by weight of a photopolymerization initiator (D); and the balance solvent (E).
The photosensitive resin composition may further include an additive (chemical polymerization initiator) of an epoxy compound (epoxy compound), malonic acid (maleic acid), 3-amino-1, 2-propanediol (3-amino-1, 2-propanediol 1), a silane-based coupling agent (silane-based coupling agent), a leveling agent (1-developing agent), a surfactant (surfactant), a radical polymerization initiator, or a combination thereof.
Another embodiment provides a photosensitive resin film manufactured using the photosensitive resin composition.
Still another embodiment provides a color filter including the photosensitive resin film.
Other embodiments of the invention are encompassed by the following detailed description.
The photosensitive resin composition according to one embodiment includes a dye within a predetermined amount range and thus can provide a color filter having excellent brightness, heat resistance, and chemical and light resistance.
Drawings
Is free of
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. These embodiments are, however, illustrative and not restrictive of the invention, and the invention is defined by the scope of the claims appended hereto.
As used herein, when not otherwise providedAs specifically defined, the term "substituted" means replaced with a substituent selected from the following, rather than a functional group of the present invention: halogen (F, Br, Cl or I), hydroxy, nitro, cyano, amino (NH)2、NH(R200) Or N (R)201)(R202) Wherein R is200、R201And R202Identical or different and independently C1 to C10 alkyl), carbamimidoyl, hydrazino, hydrazone group, carboxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted alicyclic organic group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group.
As used herein, when a specific definition is not otherwise provided, the term "alkyl" refers to a C1 to C20 alkyl group and specifically a C1 to C15 alkyl group, the term "cycloalkyl" refers to a C3 to C20 cycloalkyl group and specifically a C3 to C18 cycloalkyl group, the term "alkoxy" refers to a C1 to C20 alkoxy group and specifically a C1 to C18 alkoxy group, the term "aryl" refers to a C6 to C20 aryl group and specifically a C6 to C18 aryl group, the term "alkenyl" refers to a C2 to C20 alkenyl group and specifically a C2 to C18 alkenyl group, the term "alkylene" refers to a C865 1 to C20 alkylene group and specifically a C1 to C18 alkylene group, and the term "arylene" refers to a C6 to C20 arylene group and specifically a C6 to C16 arylene group.
As used herein, "(meth) acrylate" means "acrylate" and "methacrylate", and "(meth) acrylic acid" means "acrylic acid" and "methacrylic acid", when a specific definition is not otherwise provided.
As used herein, the term "combination" when a definition is not otherwise provided refers to mixing or copolymerization. Further, "copolymerization" refers to block copolymerization to random copolymerization, and "copolymer" refers to block copolymer to random copolymer.
In the chemical formulae of the present specification, unless a specific definition is otherwise provided, when a chemical bond is not shown at a position that should be given, the hydrogen bond is bonded at the position.
As used herein, "a" indicates a point in which the same or different atom or chemical formula is attached, when a specific definition is not otherwise provided.
The photosensitive resin composition according to one embodiment includes (a) a binder resin; (B) dyes consisting of cations and anions; (C) a photopolymerizable compound; (D) a photopolymerization initiator; and (E) a solvent, wherein the dye is included in an amount of 15 to 40 wt% based on the total amount of the photosensitive resin composition, and the cation is represented by chemical formula 1.
[ chemical formula 1]
Figure BDA0001124609760000111
In the chemical formula 1, the first and second,
R1to R6Independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group,
R7is a substituted or unsubstituted C6 to C20 aryl group, and
x is-O-, -S-or-NR8-(R8Is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group).
According to one embodiment, the photosensitive resin composition comprises a dye consisting of a cation represented by chemical formula 1 and an anion in an amount of 15 to 40% by weight based on the total amount of the photosensitive resin composition, wherein the dye has excellent spectral characteristics, a high molar extinction coefficient, and excellent coloring characteristics, heat resistance, and solubility to organic solvents such as cyclohexanone, PGMEA, etc., when the dye is included in the amount range, compared to a compound conventionally used as a colorant, for example, a triarylmethane compound. Specifically, the cation represented by chemical formula 1 has three rings connected to the carbon in the center, wherein since one of the three rings is an aromatic heterocyclic ring including a cyano group, the photosensitive resin composition including the dye composed of the cation represented by chemical formula 1 and the anion within the amount range can provide a color filter having excellent brightness, heat resistance, chemical resistance, and light resistance.
Hereinafter, each component is described in detail.
(B) Dye material
As described above, the photosensitive resin composition according to one embodiment includes a dye composed of a cation and an anion, and the cation is represented by chemical formula 1.
For example, X may be-O-or-S-.
For example, R1To R4Independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.
In order to manufacture a color filter having excellent heat resistance, light resistance, and chemical resistance as well as high luminance, research to achieve heat resistance, light resistance, and chemical resistance and high luminance of the color filter has recently been conducted by synthesizing a dye having excellent durability instead of a pigment and using a composition including the dye. Specifically, for dyes, triarylmethane compounds known as blue dyes are being studied in large quantities. Triarylmethane dyes have high brightness in the wavelength range of 420 nm to 450 nm, but have insufficient solubility in organic solvents such as PGMEA, and are inferior in heat resistance, light resistance, and chemical resistance. In order to overcome poor heat resistance and the like, there have been attempts to use anions such as naphthalenesulfonic acid, naphthylaminesulfonic acid and the like as triarylmethane dyes, but heat resistance and the like have not been greatly improved.
The dye included in the composition according to one embodiment includes a cation represented by chemical formula 1, and thus, has excellent spectral characteristics, a high molar extinction coefficient, excellent coloring characteristics, heat resistance, light resistance, and chemical resistance, and excellent solubility in organic solvents such as cyclohexanone, PGMEA, and the like, as compared to dye compounds conventionally used as colorants, such as triarylmethane compounds. Specifically, the dye included in the composition according to an embodiment has three rings connected to carbon in the center, wherein the composition of an embodiment can provide a color filter having excellent heat resistance, light resistance, and chemical resistance and high luminance because one of the three rings is an aromatic heterocyclic ring including a cyano group.
For example, the cation may be represented by chemical formula 2.
[ chemical formula 2]
Figure BDA0001124609760000121
In the chemical formula 2, the first and second organic solvents,
R9and R10Independently a substituted or unsubstituted C1 to C20 alkyl group,
R11and R12Independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R13is a substituted or unsubstituted C6 to C20 aryl group,
R14to R17Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
n1 to n4 are independently integers in the range of 0 to 5, 0. ltoreq. n1+ n 2. ltoreq.5 and 0. ltoreq. n3+ n 4. ltoreq.5, and
x is-O-or-S-.
For example, n1 through n4 may be independently an integer of 0 or 1.
For example, the halogen atom may be F, Cl, Br or I.
For example, the cation may be represented by a selected one of chemical formulas 3 to 7.
[ chemical formula 3]
Figure BDA0001124609760000131
In the chemical formula 3, the first and second,
R18、R19and R21Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
[ chemical formula 4]
Figure BDA0001124609760000132
In the chemical formula 4, the first and second organic solvents,
R18to R21Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
[ chemical formula 5]
Figure BDA0001124609760000141
In the chemical formula 5, the first and second organic solvents,
R18and R19Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R27is a substituted or unsubstituted C6 to C20 aryl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
[ chemical formula 6]
Figure BDA0001124609760000142
In the chemical formula 6, the first and second,
R18and R19Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R27and R28Independently a substituted or unsubstituted C6 to C20 aryl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
[ chemical formula 7]
Figure BDA0001124609760000151
In the chemical formula 7, the first and second,
R18、R19and R21Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R28is a substituted or unsubstituted C6 to C20 aryl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
For example, the cation may be represented by one of chemical formula 3-1, chemical formula 3-2, chemical formula 4-1 to chemical formula 4-3, chemical formula 5-1 to chemical formula 5-8, chemical formula 6-1 to chemical formula 6-19, and chemical formula 7-1 to chemical formula 7-17, but is not limited thereto.
[ chemical formula 3-1]
Figure BDA0001124609760000152
[ chemical formula 3-2]
Figure BDA0001124609760000161
[ chemical formula 4-1]
Figure BDA0001124609760000162
[ chemical formula 4-2]
Figure BDA0001124609760000163
[ chemical formulas 4-3]
Figure BDA0001124609760000171
[ chemical formula 5-1]
Figure BDA0001124609760000172
[ chemical formula 5-2]
Figure BDA0001124609760000173
[ chemical formulas 5-3]
Figure BDA0001124609760000181
[ chemical formulas 5-4]
Figure BDA0001124609760000182
[ chemical formulas 5 to 5]
Figure BDA0001124609760000191
[ chemical formulas 5 to 6]
Figure BDA0001124609760000192
[ chemical formulas 5 to 7]
Figure BDA0001124609760000201
[ chemical formulas 5 to 8]
Figure BDA0001124609760000202
[ chemical formula 6-1]
Figure BDA0001124609760000211
[ chemical formula 6-2]
Figure BDA0001124609760000212
[ chemical formula 6-3]
Figure BDA0001124609760000221
[ chemical formulas 6-4]
Figure BDA0001124609760000222
[ chemical formulas 6-5]
Figure BDA0001124609760000231
[ chemical formulas 6-6]
Figure BDA0001124609760000232
[ chemical formulas 6 to 7]
Figure BDA0001124609760000241
[ chemical formulas 6 to 8]
Figure BDA0001124609760000242
[ chemical formulas 6 to 9]
Figure BDA0001124609760000251
[ chemical formulas 6 to 10]
Figure BDA0001124609760000252
[ chemical formulas 6 to 11]
Figure BDA0001124609760000261
[ chemical formulas 6 to 12]
Figure BDA0001124609760000262
[ chemical formulas 6-13]
Figure BDA0001124609760000271
[ chemical formulae 6 to 14]
Figure BDA0001124609760000272
[ chemical formulas 6 to 15]
Figure BDA0001124609760000281
[ chemical formulas 6 to 16]
Figure BDA0001124609760000282
[ chemical formulas 6 to 17]
Figure BDA0001124609760000291
[ chemical formulas 6 to 18]
Figure BDA0001124609760000292
[ chemical formulae 6 to 19]
Figure BDA0001124609760000301
[ chemical formula 7-1]
Figure BDA0001124609760000302
[ chemical formula 7-2]
Figure BDA0001124609760000303
[ chemical formulas 7-3]
Figure BDA0001124609760000311
[ chemical formulas 7-4]
Figure BDA0001124609760000312
[ chemical formulas 7-5]
Figure BDA0001124609760000313
[ chemical formulae 7 to 6]
Figure BDA0001124609760000321
[ chemical formulae 7 to 7]
Figure BDA0001124609760000322
[ chemical formulae 7 to 8]
Figure BDA0001124609760000323
[ chemical formulae 7 to 9]
Figure BDA0001124609760000331
[ chemical formulae 7 to 10]
Figure BDA0001124609760000332
[ chemical formulae 7 to 11]
Figure BDA0001124609760000341
[ chemical formulas 7-12]
Figure BDA0001124609760000342
[ chemical formulae 7 to 13]
Figure BDA0001124609760000351
[ chemical formulae 7 to 14]
Figure BDA0001124609760000352
[ chemical formulae 7 to 15]
Figure BDA0001124609760000361
[ chemical formulae 7 to 16]
Figure BDA0001124609760000362
[ chemical formulae 7 to 17]
Figure BDA0001124609760000371
The compound according to one embodiment includes an anion, and the anion may be represented by one of chemical formulas a to F, but is not limited thereto.
[ chemical formula A ]
Figure BDA0001124609760000372
[ chemical formula B ]
Figure BDA0001124609760000373
[ chemical formula C ]
PW12O40 3-
[ chemical formula D ]
SiW12O40 4-
[ chemical formula E ]
CF3SO3 -
[ chemical formula F ]
ClO4 -
The dye in the composition according to one embodiment may express clear color even in a small amount, and when used as a colorant, a display device having excellent color characteristics (such as brightness, contrast, etc.) may be manufactured due to the cation represented by chemical formula 1. For example, the dye may be, for example, a blue dye having a wavelength range of 600 to 700 nanometers, for example, in a wavelength range of 640 to 650 nanometers, with a maximum absorbance (λ)max) The dye of (4). For example,the dye may be of maximum transmission (T) in the wavelength range 400 nm to 500 nm, for example 420 nm to 450 nm, and for example 430 nm to 440 nmmax) The dye of (4).
In general, dyes are the most expensive of the components used in color filters. Therefore, expensive dyes may need more to achieve desired effects such as high brightness, high contrast, etc. and thus increase unit production costs. However, when the dye in the composition according to one embodiment is used as a dye in a color filter, the compound can achieve excellent color characteristics (such as high brightness, high contrast, etc.) and reduce unit production costs even when used in a small amount.
The dye may be included in an amount of 10 to 40 wt%, for example 15 to 30 wt%, based on the total amount of the photosensitive resin composition. When the compound according to one embodiment in the range is included, heat resistance, light resistance and chemical resistance and color reproducibility and brightness simultaneously become excellent.
(B') pigment
For example, the photosensitive resin composition according to one embodiment may further include a pigment.
The pigment may include a blue pigment, a yellow pigment, a green pigment, a red pigment, a violet pigment, or a combination thereof, but is not limited thereto. For example, the pigment may be contained in the photosensitive resin composition in the form of a pigment dispersion.
The pigment dispersion liquid may contain a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.
The solid pigment may be included in an amount of 1 to 20 wt%, such as 8 to 20 wt%, for example 15 to 20 wt%, such as 8 to 15 wt%, for example 10 to 20 wt%, for example 10 to 15 wt%, based on the total amount of the pigment dispersion.
The dispersant may be a nonionic dispersant, an anionic dispersant, a cationic dispersant, or the like. Specific examples of the dispersant may be polyolefin glycol and ester thereof, polyoxyalkylene, polyol ester alkylene oxide addition product, alcohol alkylene oxide addition product, sulfonate, carboxylate, alkylamide alkylene oxide addition product, alkylamine, and the like, and they may be used alone or in a mixture of two or more.
Commercially available examples of dispersants may include Disbek (DISPERBYK) -101, disbek-130, disbek-140, disbek-160, disbek-161, disbek-162, disbek-163, disbek-164, disbek-165, disbek-166, disbick-170, disbick-171, disbick-182, disbick-2000, disbick-2001, and the like, manufactured by BYK co, Ltd; effka-47, Effka-47 EA, Effka-48, Effka-49, Effka-100, Effka-400, Effka-450, etc., manufactured by Effka Chemicals Co., Ltd.; sofosspis (Solsperse)5000, Sofosspis 12000, Sofosspis 13240, Sofosspis 13940, Sofosspis 17000, Sofosspis 20000, Sofosspis 24000GR, Sofosspis 27000, Sofosspis 28000, and the like, manufactured by Zeneka Co., Ltd.; or PB711 and PB821 manufactured by Ajinomoto Inc.
The dispersant may be included in an amount of 1 to 20 wt% based on the total weight of the pigment dispersion. When the dispersant is included within the range, the dispersion of the photosensitive resin composition is improved due to an appropriate viscosity, and thus, optical, physical, and chemical qualities can be maintained when the photosensitive resin composition is applied to a product.
The solvent used for forming the pigment dispersion liquid may be ethylene glycol acetate, ethyl cellosolve, propylene glycol monomethyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, or the like.
The pigment dispersion may be included in an amount of 5 to 30 wt%, for example, 10 to 25 wt%, based on the total amount of the photosensitive resin composition. When the pigment dispersion liquid is contained within the range, a process margin can be secured, and color reproducibility and contrast are improved.
(A) Adhesive resin
The binder resin may be an acryl-based binder resin, a cardo-based binder resin, or a combination thereof.
The acryl-based binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing at least one acryl-based repeating unit.
The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group. Examples of the monomer include (meth) acrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.
The first ethylenically unsaturated monomer may be included in an amount of 5 to 50 wt%, for example, 10 to 40 wt%, based on the total amount of the acryl-based resin.
the second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene, α -methylstyrene, vinyltoluene, vinylbenzylmethyl ether and the like, an unsaturated carboxylic acid ester compound such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate and the like, an unsaturated carboxylic acid aminoalkyl ester compound such as 2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate and the like, a carboxylic acid vinyl ester compound such as vinyl acetate, vinyl benzoate and the like, an unsaturated carboxylic acid glycidyl ester compound such as glycidyl (meth) acrylate and the like, a vinyl cyanide compound such as (meth) acrylonitrile and the like, an unsaturated amide compound such as (meth) acrylamide and the like, and may be used alone or as a mixture of two or more.
Specific examples of the acryl-based binder resin may be, but are not limited to, a poly (benzyl methacrylate) copolymer, an acrylic acid/benzyl methacrylate copolymer, a methacrylic acid/benzyl methacrylate/styrene copolymer, a methacrylic acid/benzyl methacrylate/2-hydroxyethyl methacrylate copolymer, a methacrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, and the like. These may be used alone or in a mixture of two or more.
The binder resin may have a weight average molecular weight of 5,000 g/mole to 150,000 g/mole, such as 5,000 g/mole to 50,000 g/mole, such as 10,000 g/mole to 30,000 g/mole. When the binder resin has a weight average molecular weight within the range, the photosensitive resin composition has good physical and chemical characteristics, an appropriate viscosity, and close contact characteristics with the substrate during the manufacture of the color filter.
The binder resin may have an acid number of 80 mg potassium hydroxide/g to 130 mg potassium hydroxide/g, for example 90 mg potassium hydroxide/g to 120 mg potassium hydroxide/g. When the binder resin has an acid value within the range, the pixel pattern may have excellent resolution.
The binder resin may be included in an amount of 1 to 30 wt%, for example, 10 to 25 wt%, based on the total amount of the photosensitive resin composition. When the binder resin is included within the above range, the developability may be improved and excellent surface smoothness may be improved due to improved crosslinking during the manufacture of the color filter.
(C) Photopolymerizable compounds
The photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth) acrylic acid containing at least one ethylenically unsaturated double bond.
The photopolymerizable compound has an ethylenically unsaturated double bond, and thus can cause sufficient polymerization during exposure in the pattern forming process and form a pattern having excellent heat resistance, light resistance, and chemical resistance.
Specific examples of the photopolymerizable compound may be ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, bisphenol a di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol a epoxy (meth) acrylate, and the like, Ethylene glycol monomethyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate, and the like.
Examples of commercially available photopolymerizable compounds are as follows. Examples of the monofunctional (meth) acrylate may include anix (Aronix)
Figure BDA0001124609760000391
(Toagosei chemical industry Co., Ltd.); kayalard (KAYARAD)
Figure BDA0001124609760000392
(Nippon Kayaku Co., Ltd.,. Ltd.);
Figure BDA0001124609760000393
(Osaka organic Chemical industry, Ltd.) and the like. Examples of the bifunctional ester of (meth) acrylic acid may include anixol
Figure BDA0001124609760000394
(Toyo Synthesis chemical Co., Ltd.); kayalard
Figure BDA0001124609760000401
(Nippon Kagaku Co., Ltd.);
Figure BDA0001124609760000402
(Osaka organic chemical Co., Ltd.) and the like. Examples of the trifunctional (meth) acrylate may include anixol
Figure BDA0001124609760000403
Figure BDA0001124609760000404
(Toyo Synthesis chemical Co., Ltd.); kayalard
Figure BDA0001124609760000405
Figure BDA0001124609760000406
(Nippon Kagaku Co., Ltd.);
Figure BDA0001124609760000407
Figure BDA0001124609760000408
(Osaka organic chemical Co., Ltd.) and the like. These may be used alone or in a mixture of two or more.
The photopolymerizable compound may be treated with an acid anhydride to improve developability.
The photopolymerizable compound may be included in an amount of 1 to 15 wt%, for example, 5 to 10 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerizable compound is contained in the range, the photopolymerizable compound is sufficiently cured during exposure in the pattern forming process and has excellent reliability, and the developability of the alkaline developer can be improved.
(D) Photopolymerization initiator
The photopolymerization initiator is an initiator generally used in a photosensitive resin composition, and examples thereof include acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, oxime compounds, and combinations thereof.
Examples of the acetophenone compounds may be 2, 2 ' -diethoxyacetophenone, 2 ' -dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2 ' -dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one and the like.
Examples of the benzophenone-based compound may be benzophenone, benzoyl benzoate, benzoyl methyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4 ' -bis (dimethylamino) benzophenone, 4 ' -bis (diethylamino) benzophenone, 4 ' -dimethylaminobenzone, 4 ' -dichlorobenzophenone, 3 ' -dimethyl-2-methoxybenzophenone and the like.
Examples of the thioxanthone-based compound may be thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-diisopropylthioxanthone, 2-chlorothioxanthone, etc.
Examples of benzoin-based compounds may be benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.
Examples of triazines are 2, 4, 6-trichloro-s-triazine, 2-phenyl-4, 6-bis (trichloromethyl) -s-triazine, 2- (3 ', 4 ' -dimethoxystyryl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4 ' -methoxynaphthyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4, 6-bis (trichloromethyl) -s-triazine, 2-biphenyl-4, 6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphthol-1-yl) -4, 6-bis (trichloromethyl) -s-triazine (2- (naphthol-1-y1) -4, 6-bis (trichloromethyl) -s-triazine), 2- (4-methoxynaphthol-1-yl) -4, 6-bis (trichloromethyl) -s-triazine (2- (4-methoxyynohthol-1-y 1) -4, 6-bis (trichloromethyl) -s-triazine), 2-4-bis (trichloromethyl) -6-piperonyl-s-triazine, 2-4-bis (trichloromethyl) -6- (4-methoxystyryl) -s-triazine, and the like.
examples of the oxime compound include O-acyloxime compounds, 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl ] -1, 2-octanedione, 1- (O-acetyloxime) -1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethanone, O-ethoxycarbonyl- α -oxyamino-1-phenylpropan-1-one, and the like, and specific examples of the O-acyloxime compound include 1, 2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one, 1- (4-phenylthiophenyl) -butan-1, 2-dione 2-oxime-O-benzoate, 1- (4-phenylthiophenyl) -octan-1-O-acetate, and 1- (4-phenylthiophenyl) -butan-1-one oxime-O-acetate, and the like.
The photopolymerization initiator may further contain, in addition to the compounds, carbazole-based compounds, diketone-based compounds, sulfonium borate-based compounds, diazo-based compounds, imidazole-based compounds, bisimidazole-based compounds, and the like.
The photopolymerization initiator may be used together with a photosensitizer capable of causing a chemical reaction by absorbing light and becoming excited and then transferring its energy.
Examples of the photosensitizer may be tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate, and the like.
The photopolymerization initiator is contained in an amount of 0.01 to 10% by weight, for example, 0.05 to 5% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the range, excellent reliability may be ensured since sufficient curing is performed during exposure in a pattern forming process, a pattern may have excellent resolution and close contact characteristics as well as excellent heat resistance, light resistance, and chemical resistance, and transmittance may be prevented from being deteriorated due to a non-reactive initiator.
(E) Solvent(s)
The solvent is a material having compatibility with, but not reacting with, the dye, the pigment, the binder resin, the photopolymerizable compound, and the photopolymerization initiator.
Examples of the solvent may include alcohols such as methanol, ethanol, and the like; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, tetrahydrofuran, and the like; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and the like; ethylene glycol ethyl ether such as methyl ethylene glycol ethyl ether, ethyl ethylene glycol ethyl ether, diethyl ethylene glycol ethyl ether, etc.; carbitol (carbitol), such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and the like; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate and the like; aromatic hydrocarbons such as toluene, xylene, etc.; ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl n-acetone, methyl n-butanone, methyl n-pentanone, 2-heptanone, etc.; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, etc.; lactates such as methyl lactate, ethyl lactate, and the like; alkyl oxyacetates such as methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, etc.; alkyl alkoxyacetates such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate and the like; alkyl 3-oxopropionates such as methyl 3-oxopropionate, ethyl 3-oxopropionate, etc.; alkyl 3-alkoxypropionates such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; alkyl 2-oxopropionates such as methyl 2-oxopropionate, ethyl 2-oxopropionate, propyl 2-oxopropionate, etc.; alkyl 2-alkoxypropionates such as methyl 2-methoxypropionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc.; 2-oxo-2-methylpropionates such as methyl 2-oxo-2-methylpropionate, ethyl 2-oxo-2-methylpropionate and the like; alkyl 2-alkoxy-2-methylpropionates of alkyl monooxymonocarboxylates such as methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate and the like; esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methylethyl propionate, hydroxyethyl acetate, 2-hydroxy-3-methyl butyrate, and the like; ketoesters, such as ethyl pyruvate, and the like. In addition, high boiling point solvents such as N-methylformamide, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, ethyl benzyl ether, dihexyl ether, acetylacetone, isophorone, hexanoic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ -butyrolactone, ethylene carbonate, propylene carbonate, phenyl ethylene glycol ethyl acetate, and the like can also be used.
In view of mutual solubility and reactivity, glycol ethers such as ethylene glycol monoethyl ether and the like; ethylene glycol alkyl ether acetates such as ethyl ethylene glycol ethyl acetate and the like; esters such as 2-hydroxyethyl propionate and the like; carbitols such as diethylene glycol monomethyl ether and the like; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate and the like.
The solvent is used in a balance of, for example, 30 to 90 wt%, 30 to 80 wt%, 30 to 70 wt%, based on the total amount of the photosensitive resin composition. When the solvent is included within the range, the photosensitive resin composition may have an appropriate viscosity, thereby improving the coating characteristics of the color filter.
(F) Other additives
The photosensitive resin composition may further comprise additives of epoxy compounds, malonic acid, 3-amino-1, 2-propanediol, silane coupling agents, leveling agents, surfactants, radical polymerization initiators, or combinations thereof.
Specifically, the photosensitive resin composition may further include an epoxy compound to improve the close contact property with the substrate.
Examples of the epoxy compound may be a phenol novolac epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol a epoxy compound, an alicyclic epoxy compound, or a combination thereof.
The epoxy compound may be included in an amount of 0.01 to 20 parts by weight, for example, 0.1 to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is contained within the range, the close contact property, the storage capacity, and the like can be improved.
The photosensitive resin composition may further contain a silane coupling agent having a reactive substituent such as a carboxyl group, a methacryloyl group, an isocyanate group, an epoxy group, or the like, in order to improve adhesion with the substrate.
examples of the silane coupling agent include trimethoxysilylbenzoic acid, gamma-methylpropenylpropoxyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, gamma-isocyanatopropyltriethoxysilane, gamma-glycidoxypropyltrimethoxysilane, β - (3, 4-epoxycyclohexyl) ethyltrimethoxysilane and the like.
These may be used alone or in a mixture of two or more.
The silane coupling agent may be included in an amount of 0.01 parts by weight to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is contained within the above range, the close contact characteristics, the storage characteristics, and the like are improved.
The photosensitive resin composition may further include a surfactant in order to improve coating characteristics and suppress spot generation.
Examples of the surfactant may include fluorine-based surfactants, for example
Figure BDA0001124609760000421
And
Figure BDA0001124609760000422
(BM Chemie Inc.)): MEGAFACE
Figure BDA0001124609760000423
And
Figure BDA0001124609760000424
(Dainippon Ink chemical industry Co., Ltd. (Dainippon Ink Kagaku Kogyo Co., Ltd.)); fullorad
Figure BDA0001124609760000425
FULORAD
Figure BDA0001124609760000426
FULORAD
Figure BDA0001124609760000427
And FULORAD
Figure BDA0001124609760000428
(Sumitomo 3M Co., Ltd., (Sumitomo 3M Co., Ltd.).))；SURFLON
Figure BDA0001124609760000429
SURFLON
Figure BDA00011246097600004210
SURFLON
Figure BDA00011246097600004211
SURFLON
Figure BDA00011246097600004212
And SURFON
Figure BDA00011246097600004213
(ashlar Glass co., Ltd.); and
Figure BDA00011246097600004214
Figure BDA00011246097600004215
and
Figure BDA00011246097600004216
and the like (Toray Silicone Co., Ltd.,. Ltd.)).
The surfactant may be included in an amount of 0.001 parts by weight to 5 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the surfactant is contained within the range, it is possible to ensure coating uniformity, to generate no stain and to improve the wetting property of the glass substrate.
The photosensitive resin composition may further contain other additives such as an antioxidant, a stabilizer, etc. in a predetermined amount when the property is reduced.
According to another embodiment, there is provided a color filter manufactured using the photosensitive resin composition according to the embodiment.
According to another embodiment, a color filter including a photosensitive resin film is provided.
The pattern formation process in the color filter is as follows.
The process comprises coating a positive photosensitive resin composition onto a support substrate by spin coating, slit coating, ink jet printing, or the like; drying the coated positive photosensitive resin composition to form a photosensitive resin composition film; exposing the positive photosensitive resin composition film; developing the exposed positive photosensitive resin composition film in an alkaline aqueous solution to obtain a photosensitive resin film; and heat-treating the photosensitive resin film. Conditions for the patterning process are well known in the related art and will not be described in detail in this specification.
(examples)
(synthetic dyes)
Synthesis example 1: synthesis of dye represented by chemical formula 7-17-1
The compound represented by chemical formula 1-2 (1.03 g, 2.1 mmol) and the compound represented by chemical formula 2-2 (0.71 g, 2.1 mmol) were placed in a round-bottom flask under a nitrogen atmosphere, and toluene (5 g) and POCl were added thereto3(1.29 g, 8.4 mmol) and the mixture was stirred for 5 hours while slowly heating to 110 ℃. When the reaction was complete, the resultant was cooled to room temperature, extracted with Methyl Ethyl Ketone (MEK), and then cleaned with 10% NaCl, water, and 10% HCl, respectively. After removing the organic layer, the residue was dried, lithium bis (trifluoromethane) sulfonimide (1.2 g, 4.2 mmol) was added thereto, DMSO (10 g) was added thereto, and the mixture was stirred at room temperature for 30 minutes (anion exchange process). The stirred reactant was dropped into water to generate a precipitate, and the precipitate was separated via a filter. The obtained solid compound was dissolved in acetonitrile (40 g), activated carbon (3 g) was added thereto, and the mixture was stirred for 30 minutes. The activated carbon was removed via a filter, and the filtered solution was distilled and then dried to obtain a compound represented by chemical formula 7-17-1 (1.90 g, 83%).
[ chemical formulas 1-2]
Figure BDA0001124609760000431
[ chemical formula 2-2]
Figure BDA0001124609760000432
[ chemical formula 7-17-1]
Figure BDA0001124609760000433
1H NMR (solvent: CDCl)3)7.51-7.38(m，12H)，7.20-7.03(m，12H)，6.42(d，4H)，4.52-4.45(m，2H)，4.08(q，2H)，1.38(t，3H)，1.17(d，12H)
Synthesis example 2: synthesis of the dye represented by chemical formula 7-14-1
The dye represented by chemical formula 7-14-1 was synthesized according to the same method as synthetic example 1, except that the compound represented by chemical formula 1-1 and the compound represented by chemical formula 2-1 were used instead of the compound represented by chemical formula 1-2 and the compound represented by chemical formula 2-2 as starting materials.
[ chemical formula 1-1]
Figure BDA0001124609760000441
[ chemical formula 2-1]
Figure BDA0001124609760000442
[ chemical formula 7-14-1]
Figure BDA0001124609760000443
1H NMR (solvent: CDCl)3)7.57-7.51(m，3H)，7.45-7.26(m，8H)，7.10-7.05(m，9H)，6.50(bs，4H)，4.13(q，2H)，3.75(q，4H)，1.41(t，3H)，1.24(t，6H)
(preparation of photosensitive resin composition)
Example 1
Photosensitive resin compositions according to examples 1 to 3 and comparative examples 1 to 4 each having a composition shown in table 1 were prepared. Specifically, a photopolymerization initiator was dissolved in a solvent, and the solution was stirred at room temperature for 2 hours. Next, a binder resin and a photopolymerizable monomer were added thereto, and the mixture was stirred at room temperature for 2 hours. Subsequently, a dye (depending on the case, a pigment dispersion liquid) was added thereto, the mixture was stirred at room temperature for one hour, other additives (surfactants) were added thereto, and the obtained mixture was stirred at room temperature for one hour. The solution was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.
[ Table 1]
(unit: wt%)
Figure BDA0001124609760000451
(A) Adhesive resin
Acryl based binder resin (methacrylic acid/benzyl methacrylate 15/85 (weight/weight), weight average molecular weight 22,000 g/mol, acid value 100 mg potassium hydroxide/g)
(B) Dye material
(B-1) the dye represented by chemical formula 7-17-1
(B-2) the dye represented by the chemical formula 7-14-1
(B-3) the dye represented by chemical formula 18 (Win-chemical Ltd.), Brilliant Blue (Brilliant Blue) FG)
[ chemical formula 18]
Figure BDA0001124609760000452
(B') pigment
(B' -1) B15: 6 pigment Dispersion (Sanyo Ltd.)
(C) Photopolymerizable compounds
Dipentaerythritol hexaacrylate (DPHA)
(D) Photopolymerization initiator
Oxime initiator (OXE-01, BASF Corp.)
(E) Solvent(s)
Propylene Glycol Monomethyl Ether Acetate (PGMEA)
(F) Other additives
Fluorine surfactant (F-554 (10% diluted solution), DIC Co., Ltd. (DIC Co., Ltd.))
Evaluation of
Evaluation 1: brightness and heat resistance
The photosensitive resin compositions according to examples 1 to 3 and comparative examples 1 to 4 were respectively coated at revolutions per minute (rpm) at which a predetermined thickness could be obtained by using a coater (omphacat MS-a150, sankis corporation (Mikasa co., Ltd.), and pre-baked on a hot plate at 90 ℃ (before post-baking, PSB)). Subsequently, a film sample was completed by exposing the coated composition with an exposure apparatus (HB-50110AA, oxtail corporation (UshioInc.)) under an exposure condition of 50 mj/cm, and baking in an oven at 230 ℃ for 30 minutes (after PSB). Color coordinates and brightness (Y) of the film samples were measured by using the MCPD 3000 apparatus before and after the oven baking, and the results are shown in table 2, and in addition, del (E) was calculated with reference to color coordinate changes before and after PSB to evaluate heat resistance, and the results are shown in table 3.
Evaluation 2: light resistance and chemical resistance
The light fastness was evaluated by exposing the film sample in evaluation 1 to light with a xenon lamp (0.68 watt intensity) at 60 ℃ for 2 hours, the color coordinates thereof were measured by using an MCPD 3000 apparatus, the color coordinates were converted to del (E) with reference to the color coordinate change before and after PSB, and the results are shown in table 3.
Evaluation 3: chemical resistance
The chemical characteristics were measured by immersing the film sample of evaluation 1 in N-methylpyrrolidinone (NMP) at room temperature for 10 minutes and drying it. Subsequently, the chemical resistance was measured by measuring the color coordinates of the film sample with the MCPD 3000 apparatus and converting the color coordinates into del (E) with reference to the color coordinate change before and after the PSB, and the results are shown in table 3.
[ Table 2]
Figure BDA0001124609760000461
[ Table 3]
Heat resistance Light resistance Chemical resistance
Example 1 1.72 1.87 2.73
Example 2 1.31 1.7 2.87
Example 3 1.45 1.83 2.78
Comparative example 1 2.35 0.67 2.89
Comparative example 2 4.01 11.37 20.68
Comparative example 3 1.76 1.90 2.94
Comparative example 4 1.99 1.92 2.98
Referring to tables 2 and 3, the photosensitive resin compositions according to examples 1 to 3 exhibited excellent brightness, heat resistance, and chemical resistance and simultaneously exhibited excellent light resistance characteristics, as compared to the photosensitive resin compositions according to comparative examples 1 to 4.
While the invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not to be limited to the disclosed embodiments, but on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. The foregoing embodiments are therefore to be considered in all respects illustrative rather than limiting of the invention.

Claims (18)

1. A photosensitive resin composition, comprising:
a binder resin;
dyes consisting of cations and anions;
a photopolymerizable compound;
a photopolymerization initiator, and
a solvent, a water-soluble organic solvent,
wherein the dye is contained in an amount of 15 to 40% by weight based on the total amount of the photosensitive resin composition, and
the cation is represented by chemical formula 1:
[ chemical formula 1]
Figure FDA0001124609750000011
Wherein, in chemical formula 1,
R1to R6Independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group,
R7is a substituted or unsubstituted C6 to C20 aryl group, and
x is-O-, -S-or-NRa-, wherein R8Is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
2. The photosensitive resin composition of claim 1, wherein said X is-O-or-S-.
3. The photosensitive resin composition of claim 1, wherein R is1To R4Independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.
4. The photosensitive resin composition of claim 1, wherein the cation is represented by chemical formula 2:
[ chemical formula 2]
Figure FDA0001124609750000021
Wherein, in chemical formula 2,
R9and R10Independently a substituted or unsubstituted C1 to C20 alkyl group,
R11and R12Independently of a hydrogen atomA substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
R13is a substituted or unsubstituted C6 to C20 aryl group,
R14to R17Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
n1 to n4 are independently integers in the range of 0 to 5, 0. ltoreq. n1+ n 2. ltoreq.5 and 0. ltoreq. n3+ n 4. ltoreq.5, and X is-O-or-S-.
5. The photosensitive resin composition of claim 1, wherein the cation is represented by a selected one of chemical formulas 3 to 7:
[ chemical formula 3]
Figure FDA0001124609750000022
Wherein, in chemical formula 3,
R18、R19and R21Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-,
[ chemical formula 4]
Figure FDA0001124609750000031
Wherein, in chemical formula 4,
R18to R21Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently isA halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-,
[ chemical formula 5]
Figure FDA0001124609750000032
Wherein, in chemical formula 5,
R18and R19Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R27is a substituted or unsubstituted C6 to C20 aryl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-,
[ chemical formula 6]
Figure FDA0001124609750000041
Wherein, in chemical formula 6,
R18and R19Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R27and R28Independently a substituted or unsubstituted C6 to C20 aryl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-,
[ chemical formula 7]
Figure FDA0001124609750000042
Wherein, in chemical formula 7,
R18、R19and R21Independently a substituted or unsubstituted C1 to C20 alkyl group,
R22is a halogen atom, and is a halogen atom,
R23to R26Independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R28is a substituted or unsubstituted C6 to C20 aryl group,
m is an integer in the range of 0 to 2,
n5 to n8 are independently integers of 0 or 1, an
X is-O-or-S-.
6. The photosensitive resin composition of claim 1, wherein the cation is represented by one selected from the group consisting of chemical formula 5-3, chemical formula 5-4, chemical formula 5-5, chemical formula 5-6, chemical formula 7-8, chemical formula 7-10, chemical formula 7-12, chemical formula 7-14, and chemical formula 7-17:
[ chemical formulas 5-3]
Figure FDA0001124609750000051
[ chemical formulas 5-4]
Figure FDA0001124609750000052
[ chemical formulas 5 to 5]
Figure FDA0001124609750000061
[ chemical formulas 5 to 6]
Figure FDA0001124609750000062
[ chemical formulae 7 to 6]
Figure FDA0001124609750000063
[ chemical formulae 7 to 8]
Figure FDA0001124609750000071
[ chemical formulae 7 to 10]
Figure FDA0001124609750000072
[ chemical formulas 7-12]
Figure FDA0001124609750000081
[ chemical formulae 7 to 14]
Figure FDA0001124609750000082
[ chemical formulae 7 to 17]
Figure FDA0001124609750000091
7. The photosensitive resin composition of claim 1, wherein the anion is represented by one selected from the group consisting of chemical formula a to chemical formula F:
[ chemical formula A ]
Figure FDA0001124609750000092
[ chemical formula B ]
Figure FDA0001124609750000093
[ chemical formula C ]
PW12O40 3-
[ chemical formula D ]
SiW12O40 4-
[ chemical formula E ]
CF3SO3 -
[ chemical formula F ]
ClO4 -。
8. The photosensitive resin composition of claim 1, wherein the dye is a blue dye.
9. The photosensitive resin composition of claim 1, wherein the dye has a maximum absorbance in a wavelength of 600 nm to 700 nm.
10. The photosensitive resin composition of claim 1, wherein the dye has a maximum transmittance in a wavelength of 400 nm to 500 nm.
11. The photosensitive resin composition of claim 1, wherein the photosensitive resin composition further comprises a pigment.
12. The photosensitive resin composition of claim 1, wherein the binder resin has a weight average molecular weight of 5,000 to 15,000 g/mole.
13. The photosensitive resin composition of claim 1, wherein the binder resin has an acid value of 80 to 130 mg of potassium hydroxide per gram.
14. The photosensitive resin composition of claim 1, wherein the binder resin comprises an acryl-based binder resin, a cardo-based binder resin, or a combination thereof.
15. The photosensitive resin composition of claim 1, wherein the photosensitive resin composition comprises, based on the total amount of the photosensitive resin composition:
1 to 30 wt% of the binder resin;
15 to 40 weight percent of the dye;
1 to 15% by weight of the photopolymerizable compound;
0.01 to 10% by weight of the photopolymerization initiator, and
the balance of the solvent.
16. The photosensitive resin composition of claim 1, wherein the photosensitive resin composition further comprises an additive of an epoxy compound, malonic acid, 3-amino-1, 2-propanediol, a silane-based coupling agent, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof.
17. A photosensitive resin film produced using the photosensitive resin composition according to claim 1.
18. A color filter comprising the photosensitive resin film according to claim 17.
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